Shaftsbury Vermont Real Estate

Full of character and opportunity, this charming 2-bedroom, 2-bath home in Shaftsbury offers an affordable entry into homeownership or a fantastic addition to an investment portfolio. Once serving as the local post office, the property has a unique history and a cozy footprint that makes it ideal as a starter home, downsizing option, or rental property. Recent improvements include a beautifully remodeled bathroom and a new heating and hot water system installed in 2026, providing peace of mind and enhanced efficiency. Conveniently located with easy access to Bennington and Manchester, this quaint home combines small-town Vermont charm with practical updates and endless potential. A rare opportunity to own a piece of local history while enjoying comfortable, low-maintenance living. 3D Virtual Tours Available Upon Request.

Enjoy the effortless flow and convenience of single-level living in this 3-bedroom, 2-bathroom manufactured home. Thoughtfully set back above the road on a private, expansive 1+ acre lot. A long driveway leads to the property, offering enhanced privacy and curb appeal. Inside, the inviting open floor plan is anchored by an expansive kitchen with abundant storage and a bright dining nook that seamlessly connects to a dedicated laundry room with a utility sink. Generously sized bedrooms provide comfortable accommodations throughout, led by a primary suite featuring a spacious ensuite complete with a double vanity, large soaking tub, separate shower, and exceptional cabinet storage. Outside, enjoy the spacious yard and outdoor space, complete with a hot tub included with the sale.

This Charming country home is currently being used as a primary home with a vacant 2nd in-law rental home. This property could be either a single family residence with/without an in-law house or as a 2 unit multifamily with 2 separate houses, This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large living room. 3 bedrooms, including an addition with a large primary with 2 closets inlcuding one whick is a large walk-in closet. A large full bath with washer/dryer hookups completes the living area. The house has a partial concrete basement under the older portion, with a crawlspace under the addition. This main house needs some TLC including interior paint and could use new carpet and vinyl flooring. The smaller second house is located a few hundred feet from the main house and has its own separate driveway and a separate septic system (the 2 houses do share a common drilled well) This house features a 2 room design with the kitchen / living room space, large bedroom, full bath, and a utility/laundry room. At 798 sqft, there is plenty of room. There is some unresolved freeze damage to the plumbing in the 2nd house. All income figures are based on estimated rents for both houses. The property will be sold with both units vacated. A rare chance to own a property with 2 homes for the cost of one!

Nature lovers, rejoice! Situated on 23 private acres with a beautiful mountain view, this property offers exceptional privacy and seclusion surrounded by the natural beauty of Vermont. With abundant space to explore, relax, and enjoy the outdoors, it’s an ideal setting for those seeking a peaceful country retreat. The main level features a spacious open floor plan with a large kitchen and breakfast bar that flows into the dining and living areas. A generously sized first-floor primary suite includes a Jacuzzi tub and private access to the deck. First-floor laundry adds to the convenience. Upstairs, you'll find two large bedrooms and a full bath, providing plenty of additional living space. Other notable features include Andersen windows, 200-amp electrical service, a durable metal roof, and a full walkout basement featuring a workshop and excellent potential for additional storage or usable space. Priced $165,000 below the current assessed value to reflect the work and improvements needed, this property presents a rare chance to get into a sought-after neighborhood at a significantly lower price point. With plenty of upside, it offers an excellent opportunity for an investor or owner-occupant looking to build sweat equity while transforming the property into their own private Vermont retreat. Property is being sold “AS IS” and will only qualify for conventional financing, a renovation/rehab loan, or cash.

Nearly Lakefront Living in the Heart of North Bennington! Come for the space, stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600 sq. ft. primary suite, featuring energy-efficient mini-split heating and cooling, with a large main bedroom and an adjoining space ideal for a walk-in closet or private retreat. A new steel two-car garage was added, ensuring your vehicles stay protected year-round. The property’s outdoor space is just as impressive with beautifully maintained perennial gardens (featuring lilacs, peonies, lilies, and phlox), fruit trees (peach and plum), and graceful white birches. A small backyard storage shed with electricity adds extra convenience. Located just steps from picturesque Lake Paran and nestled in the charming Village of North Bennington, this home offers the perfect balance of peaceful village life and easy access to nearby commercial areas. Plus, inclusion in the North Bennington Graded School District allows PreK through 6th grade students to attend an approved independent or private school tuition-free. Don’t miss the opportunity to enjoy this rare combination of space, location, and community!

Set on 2.5 beautiful acres, this inviting Cape-style home offers a wonderful combination of comfortable living space, character, and versatile outbuildings. The primary suite is conveniently located on the main level, with two additional bedrooms and a full bath upstairs. An attached two-car garage provides convenient parking and additional storage. The spacious living room features wide pine floors, built-in cabinetry, a fireplace, and a slider leading to the deck. The dining room continues the charm with wide pine flooring, a large window, and a built-in corner cabinet. Outside, the property offers a large barn with two stalls and an expansive workshop, along with two additional sheds for plenty of storage. There is also the possibility of restoring the property's former pond, adding another attractive feature to the landscape. The kitchen is ready for renovation, offering an opportunity to create a space tailored to your own style and needs. With 2.5 acres, a barn, workshop, attached two-car garage, and plenty of potential, this property is ready for its next chapter.

Open House September 6 Sunday Noon to 2 Welcome to 1111 Old Depot Road in Shaftsbury, Vermont, where country living and natural beauty come together on approximately four scenic acres. This inviting four-bedroom, two-full-bath ranch-style home offers a rare opportunity to enjoy privacy, natural beauty, and convenient access to one of Southern Vermont's most beloved recreational destinations. Set on a spacious parcel with room to relax, garden, and explore, the property provides a peaceful setting surrounded by mature trees and open space. The home's comfortable layout offers easy single-level living, making it ideal as a primary residence, vacation getaway, or investment property. A true highlight of the property is its proximity to the Lake Shaftsbury area, where residents can enjoy swimming, fishing, kayaking, paddleboarding, hiking, and year-round outdoor recreation just moments away. Whether you're enjoying a quiet morning surrounded by nature, spending the afternoon on the water, or gathering with family and friends around a backyard fire, this property embraces the Vermont lifestyle in every season. Conveniently located near the historic communities of Shaftsbury and Bennington, you'll enjoy easy access to shopping, dining, cultural attractions, and local services while maintaining the tranquility of a country setting. Nearby parks, trails, and recreational opportunities further enhance the appeal of this special location. Offering four bedrooms, two full baths, four acres of land, and a unique setting near Lake Shaftsbury, 1111 Old Depot Road presents an exceptional opportunity to own a Vermont home where recreation, relaxation, and natural beauty are part of everyday life.

Set privately on 25.34 acres, this 3BR/2BA contemporary-style home offers expansive views and a peaceful setting just 15 minutes from Bennington. Kitchen with breakfast nook opens out onto a back deck and the spacious living room features a cathedral ceiling and dramatic floor-to-ceiling fieldstone fireplace, creating an impressive focal point and inviting gathering space. First floor also includes a formal dining room and first floor bedroom or office as well as a full bath. On the second floor, the primary suite includes a large bathroom with a walk-in shower and tub, with a layout that may accommodate accessibility needs and a second guest bedroom includes a half bath. Basement-level 2-car garage provides workspace and a dedicated laundry area. The property offers a wonderful combination of privacy, acreage, and convenience, with plenty of room to enjoy nature and and the surrounding landscape. There is ample room for gardening and play! The home needs some repairs and updating, providing an opportunity for the next owner to make improvements and build value over time. With its desirable location, expansive views, substantial acreage, and distinctive architectural features, this property offers excellent potential for future investment and personalization.

Some homes simply have a way of making you slow down. Built in 1863, the original Twitchell Farmhouse is one of them. Rich in history and craftsmanship, this beautifully maintained four-bedroom, 2.5-bath home offers the warmth and authenticity that only a true Vermont farmhouse can provide. Original hardwood floors, handcrafted woodwork by a master carpenter, and thoughtful updates create a home that feels both timeless and comfortable. The country kitchen has been tastefully renovated while respecting the home's heritage, and the spacious primary bath features a generous double vanity with classic farmhouse styling. Whether it's curling up beside the fireplace on a snowy evening, enjoying a quiet morning in the bright enclosed sunroom, or unwinding on the private back yard surrounded by gardens, every space invites you to linger just a little longer. Outside, the property's agricultural roots remain proudly intact. The impressive tri-level hand-hewn and pegged barn, with silo, offers exceptional space for hobbies, storage, or a workshop, with the original cow stanchions still in place as a reminder of its working past. The attached two-car garage, once the home's summer kitchen, adds yet another layer of character and history. Perennial gardens, heirloom lilacs, and berry bushes create colorful seasonal displays, while protected land bordering the northern boundary helps preserve the peaceful setting for years to come. Offered fully furnished and move-in ready, this remarkable farmhouse is ready to be enjoyed from the moment you arrive. Equally appealing as a cherished full-time home, a Vermont escape, or an income-producing vacation rental, it offers a rare combination of history, craftsmanship, and enduring New England character that is increasingly difficult to find.

Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability. The updated kitchen with granite couuntertops flows into an open dining and living area highlighted by soaring cathedral ceilings, creating a bright and airy atmosphere ideal for both everyday living and entertaining. A spacious family room provides additional gathering space, while the main-floor primary suite offers ease and privacy. An outdoor pellet furnace adds energy efficiency, complementing the home’s practical upgrades. Attached to the rear of the home is an 18x24 workshop/storage area-perfect for hobbies, equipment, or additional workspace. Outside, enjoy a paved driveway leading to a detached two-car garage, along with a 12x28 Shelter Logic portable garage for extra storage. A large private deck overlooks the peaceful surroundings, ideal for relaxing or hosting, and a storage shed adds even more versatility. A wonderful opportunity to enjoy private country living with generous space, thoughtful amenities, and a convenient location.

Discover a true Vermont lifestyle at this meticulously maintained charming farmhouse nestled on picturesque Shaftsbury Hollow Road. This property combines historic character with thoughtful modern updates, offering a serene retreat with breathtaking mountain views across a just shy of 10-acre lot where the White Creek gracefully runs along one side and the entire back boundary. Step out onto the brand new 400 sq. ft. deck, perfectly positioned to capture panoramic vistas, ideal for entertaining or simply enjoying quiet moments. Inside, a versatile new addition provides flexible space that can effortlessly serve as an additional bedroom, a dedicated home office, or a bonus room to suit your needs. Every detail reflects the current owners' dedication, ensuring a move-in ready experience. The property also boasts a beautiful barn, offering ample space for storage or animals, alongside a well-established fenced raised bed garden. Embrace sustainable living with your very own owned solar system located in the yard, providing energy efficiency and reduced utility costs.

Well designed and newer home on 10.085 acres in Shaftsbury, VT. Offering 3 bedrooms, including main level primary bedroom and 2 full bathrooms. Cathedral ceiling formal dining room and modern kitchen with dining area and breakfast bar. Large living room with vaulted ceiling and lots of light. Main level laundry and rear mudroom finish the first floor. Upstairs there is a wonderful loft area, 2 more bedrooms and a full bathroom. The basement is large and could possible have finished space. The outside is where this home truly shines. Great location, large sitting porch to watch the fauna. Rear deck for relaxing and large yard space. Large barn for either shop work or you could use it as a garage, as well as a storage shed. Short walk to the creek and lots of hiking trails.

Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior, particularly in the two full bathrooms, which now showcase exquisite glazed Italian subway tiles, natural river stones, and other elegant natural surfaces, creating spa-like environments. A recently added Danish wood stove promises cozy evenings and efficient heating, adding to the homes inviting ambiance. One of the three bedrooms has been artfully transformed into a versatile library/office. This beautiful space is perfect for quiet contemplation or remote work, and is designed to gracefully accommodate overnight guests, offering both comfort and privacy. Enjoy the expansive Vermont outdoors from the generous deck spanning the back of the house, with direct access from the master bedroom – an ideal spot for morning coffee or evening stargazing. The 6.8-acre property offers ample space for privacy and connection with nature, embodying the best of rural living.

Set on 3 beautiful acres with fabulous views in every direction, this spacious and inviting home offers a wonderful blend of comfort, character, and versatility. The main level features a private primary bedroom, a large kitchen, and a welcoming living room with hardwood floors and a fireplace with woodstove insert. A generously sized office with built-ins provides the perfect space for working from home or a quiet retreat. The sunroom, located just off the back of the house, is an ideal spot to relax and enjoy the surrounding scenery throughout the seasons. The lower level offers three additional bedrooms, a full bath, and a spacious family room with another fireplace. Walk out directly to the patio and beautifully landscaped grounds, where you'll find established perennial gardens and fruit trees. There is plenty of room for gardening, entertaining, or simply enjoying the peaceful setting and expansive views. An attached two-car garage is conveniently located on the main level, while an additional garage on the lower level provides a workshop area and houses the utilities. With its flexible floor plan, abundant living space, spectacular views, and beautiful grounds, this property offers a wonderful opportunity to enjoy country living at its best.

Welcome to the Fox Hill Community and a beautiful modern home tucked away on a private road in Shaftsbury, Vermont offering the perfect blend of privacy, comfort, and stunning Vermont scenery. The home offers 3 bedrooms and 3 bathrooms along with gorgeous mountain views. There is a cozy fireplace in the living room with ample space provided for a family, friends and entertaining. The landscaping is built around the property to accent the outdoors as a beautiful, serene retreat. Whether you're entertaining outdoors, unwinding by the fire, or taking in the breathtaking views, this home offers a lifestyle that's hard to match. Contact me today to schedule your private showing and experience this exceptional property for yourself!

Vermont Home with Mountain, Meadow and Garden views Nestled in the Green Mountains of Vermont, this 3 bedroom 3 bath home offers scenic views, open spaces, and the tranquility of Vermont living. Situated on three separately surveyed lots, the beautifully maintained property features Heirloom apple trees, park like forests and lush perennial gardens bursting with color throughout the seasons and ample room to enjoy the outdoors. The property is conveniently located across from Lake Shaftsbury State Park ideal for hiking, swimming, fishing, making it an ideal year-round retreat with 5 Ski Resorts with in an hour drive. Inside, the thoughtfully designed home features an open-concept main floor centered around a cozy fireplace, creating a warm and inviting gathering space. A bright sunroom opens up to the second deck overlooking gardens and heirloom apple trees. Providing the perfect spot for relaxing, reading, or enjoying nature views. The finished basement offers additional living and entertainment space with a full kitchen and three quarter bath, while the enclosed loft on the second floor provides flexibility as a third bedroom, home office, studio, or guest area. Whether you're seeking a primary residence, a vacation getaway, or a property with room to grow, this charming Vermont home combines comfort, character, and natural beauty in an exceptional setting.

The Dexter Road Farmhouse, Circa 1800 In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic nearby backroads to write “Stopping by the Woods on a Snowy Evening." Dating back more than 225 years, this charming farmhouse offers a rare opportunity to own a piece of Vermont history while embracing the slower pace and natural beauty that define the region. Tucked away at the end of a peaceful, tree-lined town road, the property is ideally suited as a second home, creative retreat, or year-round residence. Lovingly cared for by the same family for over 70 years, the home retains much of its original character and craftsmanship. Wide pine floors, original moldings, classic woodwork, traditional wall and ceiling boards, and a gracious entrance hall create a warm and authentic farmhouse atmosphere. Set on approximately 40 acres with a picturesque skating pond, the property offers abundant space to explore, garden, walk, and enjoy the pastoral surroundings. Writers, artists, and those seeking respite from city life will appreciate the quiet setting, changing seasonal views, and inspiring natural landscape. Whether painting, writing, working remotely, or simply unwinding, the setting encourages creativity and reflection. The spacious floor plan includes four bedrooms, three bathrooms, an inviting country kitchen, formal dining room, living room with wood-burning fireplace, library, and bonus room. A bright office overlooking the pond includes a Murphy bed, providing flexible space for guests, a studio, or a private workspace. Offering exceptional privacy while remaining convenient to the cultural, recreational, and dining attractions of Vermont's Northshire region, this remarkable property presents a rare opportunity to own a true Vermont retreat. With a town trail right out your back door, snowshoeing and cross-country skiing opportunities are close at hand. Bromley and Stratton Mountain ski resorts are within a 40 minute drive.

Nestled in a peaceful five acre setting just minutes from the shopping, dining, and everyday conveniences of both Bennington and Manchester, this beautifully maintained home offers privacy, comfort, and accessibility. Thoughtfully updated, this home offers a timeless, inviting style designed to feel welcoming for years to come. The newly renovated high end kitchen is both beautiful and functional, while two spacious primary en-suites provide exceptional flexibility and privacy. The first floor primary suite wing is a true retreat, featuring a luxurious bathroom with marble tile, frameless glass shower, double vanity and walk in closet. Upstairs, the brand new second primary ensuite offers an impressive private living area, spa like full bath, and generous closet space, perfect for guests, extended family, or a luxurious personal retreat. The inviting living room features a gas fireplace, creating a warm and comfortable space for relaxing and entertaining. The kitchen and dining area flow seamlessly into a spectacular, light filled great room with soaring 14 foot ceilings, recessed lighting, and a freestanding gas stove. Step outside and enjoy the peaceful surroundings from the charming rocking chair front porch, perfect for morning coffee and taking in the beauty of nature. The rear deck, complete with a retractable awning, provides an ideal spot for grilling, entertaining, or simply enjoying the beautifully landscaped gardens. Recent updates provide comfort, efficiency, and peace of mind, including heat pump systems (2023-2024) for efficient heating and central A/C, a new Rinnai on demand propane boiler for hot water and backup heat (2025), and a new well pump (2025). Additional features include a water softener system and a full basement offering excellent storage and utility space. With its beautiful updates, versatile floor plan, exceptional primary suites, and inviting indoor and outdoor spaces, this turnkey property is ready to welcome you home.

Gorgeous, renovated Colonial offering exceptional flexibility, thoughtful design, and timeless charm. This beautifully updated property features a spacious main residence along with a stunning addition that includes a full in-law suite and a private studio above ideal for guests, extended family, a home office, or potential rental income. Solar panels installed above the garage power efficient mini-split systems, and a Tesla Powerwall provides added energy independence and peace of mind. The main house offers four bedrooms, a fabulous chef’s kitchen with quality finishes and generous workspace, and warm, inviting living areas filled with abundant natural light. Magnificent views of Mount Anthony and the sweeping five-acre meadow below can be enjoyed from the kitchen, dining room, living room, and screened porch-where wildlife is often part of the daily landscape. A new large enclosed porch further expands the living space, creating the perfect setting to relax or entertain year-round. Set on 17+ picturesque acres framed by classic stone walls, the property offers lovely views, open meadow, and wooded privacy with ample outdoor space to explore and enjoy. A three-car detached garage provides excellent space for vehicles, storage, or hobby use, while a workshop and spacious woodshed add exceptional functionality. Equestrian enthusiasts will appreciate the charming pony barn and paddock, completing this truly special setting. A rare opportunity to own a beautifully expanded home with multiple living options, sustainable features, and breathtaking views in a serene and private landscape.

Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, an oversized 2 car garage, top notch equestrian facilities, a trout pond, playhouse and the list goes on and on. The winding driveway leads one to an enchanting compound, as it opens to overlook the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF home boasts 10 foot ceilings, with reclaimed antique oak pocket doors from a nearby mansion, inlaid floors, stained glass windows, arches and a custom cherry and granite eat in island kitchen. The foyer, gracious leads to the expansive living room and kitchen overlooking the fantastic spring fed pond... there is a main level primary suite, and second floor gathering space with pond-side balcony and 2 bedrooms. The finished basement hosts a family recreation room and a sauna. Equestrian facilities are comprised of a recently built barn with 4, 12 X 12 stalls boasting ThuroBed Matress Systems, as well as a 12 X 18 foaling stall, leaving room for additional stalls. Paddocks and pastures with Ramm Flex Fencing and a USDF regulation 20m X 60m dressage arena with sand and fiber footing. There's a large shed and a 5 acre pasture. There's so much room for storage or lifestyle expansion within the main house or the building hosting the detached garage and guest house as there is a full unfinished second floor that could expand studio, exercise and office needs. This special location is convenient to area amenities yet a total feel of being away from it all! Whether you are an equestrian, or you are looking for an idyllic homestead, a place to enjoy nature and peace, and/or a property that demonstrates Vermont beauty, one shall adore this property. It is conveniently 3 hours from NYC, 1 hour from the Albany airport, and 25 minutes from Manchester, all while still feeling a world away! West Mountain Views are engaged wherever one is on the property!

Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the landscape, framing two picturesque ponds and twin orchards that offer seasonal beauty and fresh harvests. The outdoor amenities elevate this property into a private resort: an inviting in-ground pool, hot tub, propane fire pit, and an impressive 90-foot deck with retractable awning, ideal for effortless entertaining and long summer evenings under the Vermont sky. For collectors, hobbyists, or outdoor enthusiasts, the property offers exceptional versatility. A detached four-bay garage with second-story loft provides abundant storage, while an additional outbuilding easily accommodates a large Class A motor home or boat. Separate pump houses serve both the pond and pool, ensuring functionality meets convenience. A dramatic post-and-beam great room addition, completed in 1997, creates a striking focal point within the home. Anchored by a soaring floor-to-ceiling stone fireplace, this grand yet welcoming space captures the essence of rustic elegance. Above, a charming loft offers the perfect reading nook, studio, or private office retreat. The renovated kitchen blends contemporary appliances and thoughtful design with the warmth and character of the original barn structure. Three spacious bedrooms and three beautifully updated bathrooms, including one featuring a luxurious steam shower, provide comfort and privacy for family and guests. Hidden Ponds Farm is a rare and remarkable offering, a timeless estate where history, natural beauty, and modern living come together in one unforgettable property.